


Sissy That Walk

by PilDoor



Series: Garter Slips and Cookie Dough 'Verse [2]
Category: Supernatural
Genre: Chubby Dean, Dean in Lingerie, Dean in Panties, Drag Queen, Drag Queen Benny, Drag Queen Crowley, Drag Queen Dean, Established Castiel/Dean Winchester, Established Relationship, Garter Slips and Cookie Dough Verse, Humor, M/M, What Have I Done, anal sex (implied), i don't know why i did this
Language: English
Status: Completed
Published: 2016-04-16
Updated: 2016-04-16
Packaged: 2018-06-02 15:21:51
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,424
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6571408
Author URL: https://archiveofourown.org/users/PilDoor/pseuds/PilDoor
Summary: <blockquote class="userstuff">
              <p>Dean's penchant for panties is revealed and <em>apparently</em> Charlie understands that as a dying wish for him to become a drag queen.</p>
            </blockquote>





	Sissy That Walk

Dean sees his friends from where he’s standing in line. Cas is shuffling towards them, book in front of his face because the fucker ‘forgot’ to do his homework (forgot = would rather fuck Dean in the shower) and he nearly falls when he walks into the bench the others are sitting on. 

Dean bursts out laughing, which is awkward because his friends are too far away to hear him, and the girl in front of him frowns at him. 

He’s not sure why they’re in the cafeteria – in his opinion they’re too _cool_ for the cafeteria, but here they are, so he guesses not.

He slams his (honest-to-god) tray on the table and sits down next to Benny and Cas. He places a white chocolate chunk cookie on top of the open page of Cas’ book and the dark-haired man finally looks up. 

He grabs Dean’s sleeve, a finger stroking his bicep and smiles like he’s high, but that's just love, “Thanks,” and then he leans in and kisses Dean, and that’s why Dean bought him baked goods in the first place.

“Wow-wait, what the fuck?!” Jo interrupts them, hands held out in a ‘hold the fuck up’ gesture. 

Charlie smirks, “Told ya. You guys owe me 20 bucks.”

Benny groans, “You’re practically Dean’s confidante, it’s not fair. You don’t get to play next time!”

“She doesn’t get to bet on the next time Dean and myself start dating?” Cas smirks sarcastically. 

Benny rolls his eyes, “No, but when we start betting on… I don’t know, when you’ll get married or something.”

Dean chokes on his grilled cheese and Cas carefully pats his back. He looks thoughtful, but Dean knows that he’s a little shit. 

“I think you’d look gorgeous in a veil, baby.”

Dean almost dies. “Stop! Are you trying to turn me into a cross-dresser or something?”

Charlie gasps, “Oh my god! You’d make the best drag queen ever! Can I do your makeup?”

Dean thuds his head against Cas’ shoulder, “How did this happen?”

 

X

 

There has to be explanation but Dean can't think of it as he finds himself and Benny dragged down to Rainbow by Charlie on Saturday afternoon, because apparently they have ‘open drag’ later that night, and Charlie wants to introduce them to someone.

The first things Dean notices are feathers and glitter and then he’s almost hit in the face with a giant fan that someone is dancing with. 

Charlie pulls the two guys over to a mirror where an overweight man is _covered_ in powder. He doesn’t have any eyebrows so he looks perpetually confused. He sees Charlie through the mirror and turns around to smile at her, “Long time no see, hon, how’s it going?” 

Coming face to face with the older man Dean notices that he _does_ in fact have eyebrows, they’re just covered with power or concealer or whatever the fuck.

“These are my friends, Benny and Dean,” Charlie gestures towards them.

“What a lovely couple’a fellas. I’m Crowley. Or you may get to know me more as Ms. Rainbow. I’m the foundress of this club.”

Benny and Dean mutter pleasantries.

“You boys have never done drag before?” Crowley – or Ms. Rainbow asks. 

They both shake their heads.

“Well! Lilith and Ruby, come over here,” two lanky men in various stages of makeup and dress come over, “You’ll be darlings and see to getting these fellas ready for tonight, won’t you? Thanks,” Crowley ‘muas’ air kisses at them and turns back to Charlie.

Dean turns to Benny but he is being dragged away by one of the other guys. So Dean turns around to be met with quite the predatory look of the other guy.

“Uhh,” Dean gets out intelligently.

“Hello, Dean was it? I’m Ruby, well that’s my stage name anyway, and _I’ll_ be your _mama_!” He says dramatically, making something Dean can only describe as jazz hands. He’s not sure what a ‘mama’ is, but he hopes it isn’t considered cheating. 

Ruby just shows Dean around, piles stuff into his arm and gives him a time he has to be back at the club tonight, and Dean thinks he’s more confused now than when he got there. 

He meets Benny who looks just as dazed, and Charlie who looks like she’s just heard the best joke ever, and Dean can’t help but feel like the butt of it, at the exit. 

“Oh, and remember to cinch your waist, honey!” Ruby yells when they’re halfway across the parking lot and Dean gets even more confused. 

X

“Your 'mama' give you a bunch of shit too?” Benny asks from his seat in shotgun. 

Dean nods, “Yeah, and I don’t really know why. I don’t know how to do makeup or put on a wig or anything. Ruby wasn’t actually helpful.”

Benny sighs, “Nah, Lilith either. I’m gonna go home and practice the false eyelashes all afternoon.”

Dean thinks that that’s probably a good idea. But he’s pretty sure he saw something that looked a lot like a corset of some sort in the mass of items he’d been given, so he’ll probably just get fucked in that all afternoon, rather than practice makeup. Hey, it’s not his fault his boyfriend is a freak.

“You got stockings, Dean, so if Cas is home you probably won’t get much practice done,” he can hear the fucking smirk on Charlie’s face. Why did he have to go and tell her those things anyway? Benny laughs from next to him. And why did she have to tell all of their friends?

“Shut up!”

X

There is cum running down his leg so he stuffs some paper between his butt cheeks to keep from ruining the thigh-highs plastered to his legs. He glares playfully at Cas, “You made me late. You have to help me with this makeup shit now.”

Cas is still lying naked on the bed, not looking like someone who’s about to move, “I will in a minute, I’m not over this orgasm yet.”

Dean rolls his eyes, and starts on the padding. He’s fucking screwed and it’s going to be embarrassing as all hell, but luckily his boyfriend is used to seeing him in women’s clothes, and his best friend will be right next to him on that stage. _And_ he’ll be unrecognizable under piles of makeup.

He moves the weird foam padding stuff around and huffs in irritation. He’s a sweaty and cum-filled mess, couldn’t he just add glitter and be the perfect drag queen?

Cas comes up behind him and places his hands over Dean’s, “Relax, baby. Don’t worry about padding. We’ll cinch your waist a little, it’ll be fine.”

Dean huffs, “What, because I’m already fat?!” and instantly feels like, if the other queens and the audience could see him right now, he’d win.

“Dean, I know you’re a crazy OCD perfectionist, but it’s your first time and you said you were only doing it for laughs, so you really need to stop taking it so seriously.” Cas is taking the foam-pillows out of Dean’s hands, discarding them on the floor. And Dean swallows. What did he do to deserve a man like Cas, anyway?

“Come on, let me help you with the makeup and then we’ll get you dressed,” he pulls on Dean’s hand, dragging him into the bathroom where the light is better.

“You know this stuff?” Dean asks. He’s looking at the case Ruby had given him. He has no idea what to use for what, or which colors or anything. 

“I’ve done my sister’s makeup a few times. I used to be really twink-y back in high school,” Cas glimpses up to catch the surprised look on Dean’s face. He shrugs, “It was an aesthetic thing.”

“You used to be a bottom???” Dean’s eyes nearly bulges out of his head, he’s sure.

Cas laughs, “No, baby, I was a virgin until I met you, remember?”

And that can’t be right. When they’d met back in their sophomore year of college, Cas was already being objectified on the daily, so that couldn’t be. Could it? “What the fuck?”

Cas gestures for Dean to sit down on the lidded toilet, so he does, “Come on, I must’ve told you this?”

Dean is pretty sure he hasn’t. He feels oddly proud, and then kinda disgusted with himself for being proud over something like _that_. “Wow, you must think I’m a royal slut.”

“Everybody knows you are. But I did sleep with like three people in the year after, before we started sleeping together regularly. Or no, just two,” Cas smears something on Dean’s face, he has no idea what it is. 

Dean just hums his understanding. Cas goes into the living room to get his laptop which he sets on the floor, and pulls up a 'Sickening Drag Queen Make Up Tutorial' video on youtube.

“Contouring your face is going to be so easy, you have the most chiseled features in the world,” Cas is brushing some cream all over Dean’s face. Again, he has no idea what it is. 

“Shut up, I have a double chin.” 

He feels the brush on that next, “Thanks for reminding me,” Cas snickers.

“I hate you.”

“Sssh, I’m trying to conceal the bags under your eyes.”

It’s close to an hour later, Cas is covered in powder, and Dean’s eyes are red from being poked with eyeliners, mascara wands and eyelashes, and they’ve had to reapply his lipstick five times because they kept making out, but they’re finally done.

X

They get to the club at 9pm, which is three hours later than when Ruby had asked him to be there, but Cas is a really good kisser and he also gives amazing blowjobs, so Dean doesn’t even care to come up with excuses.

“Oh, you’re already ready, thank the lord!” Ruby sighs dramatically. She’s wearing a huge red wig, that kind of reminds Dean of those judge wigs or whatever, and a red dress with a huge slit showing off her entire thigh, and red shoes with a huge platform and heel. 

Dean is wearing kitten heels and he feels like a lesbian.

“Was I not supposed to be ready when I got here?” he ignores the way Ruby checks out Cas. And he also ignores how everybody else backstage checks out Cas.

“Yeah, but I didn’t know if you’d need help. You look absolutely adorbs though. Well done on the cinching.”

“Uh, thanks.” 

“Now come on, we have to fit you into the program. What song do you wanna lip sync?” Ruby is already walking away so Dean gives Cas a frantic kiss goodbye and hurries after her.

Cas goes out to the bar where Charlie and Jo are. Dean wishes he could have made a stop by the bar before coming back here.

“I don’t know, I was thinking Kansas.” Dean wobbles after the redhead who towers over just about everyone. He has to balance on the tiny heels and with a very heavy and thick pony-tailed wig on top of his head too. It’s brown and he appreciates the natural color, especially when he catches something piss-yellow out of the corner of his eye.

“Hm. _I_ was thinking Britney.” Ruby ponders. She’s flipping through the folder with all the songs.

Dean doesn’t pay much attention; he’s pretty sure Ruby is just going to pick one for him anyway. He looks around him. Crowley is wearing a blue and white wig and something alike a ball gown. He catches sight of Benny, finally, and sees that the slutty attire Dean was gifted was just for him, and not a newbie thing. Benny is wearing a floor length dress with off the shoulder short sleeves in a very electric teal that makes the auburn of his wig seem faded. The feathers attached to his back make up for it though, and Dean feels self-conscious. Benny is quite clearly wearing padding on his ass and it makes him not look like a fat dude in a dress, so Dean is jealous.

He was given a tiny dress that just covered his fucking ass, and if he wasn’t completely tucked (thanks, Cas) his dick would’ve been hanging out. If he hadn’t cinched his waist his stomach probably would have made it rise more too. And then the garters and thigh-highs and a giant purple feather boa. 

 

It gets decided that Dean and Benny are to go on stage together, lip syncing to [Beautiful Liar](https://www.youtube.com/watch?v=QrOe2h9RtWI) by Beyoncé and Shakira, which is a song Dean’s pretty sure neither of them has ever heard.

So they’re introduced as Miss Glitora Clitora and Madame Glamorama D-Lite, names based on birthdays and front letters and Dean doesn’t remember who is who but then they’re on stage.

And Dean is a charismatic guy, he really is. He doesn’t mind meeting new people and he participates in in-class discussions, but the sound of the audience paired with the spotlight proves too much. 

Benny is walking around, rolling his shoulders and hips to the introductory tunes of the song, and Dean. Just. Stands. There. 

The crowd is cheering at first, but then they realize that Dean is a moron and some start booing and Benny finally looks behind him to see his stage sista frozen in place.

He dances towards him, lips still mouthing the words he doesn’t know, and he shakes his ass, making the huge feathers dance and the audience hollers again.

Benny starts pulling on Dean’s boa and the feel of the soft feather against his bare shoulders seem to get him out of the daze, and he looks at Benny who smiles at him in encouragement, and Dean finally starts lip syncing, making the booing stop. Then he starts cat-walking, shimmying the boa around his shoulders and waist and the audience erupts in delight. 

When Dean catches Cas’ eyes he makes a slut-drop right in front of him, and the crowd goes WILD. Dean keeps his attention on Benny for the rest of the song though.

In the end it turns out to be a lot of fun, and Benny and Dean are invited back as a duo the next week. They even make 100 dollars between them, which they instantly buy shots with, and everyone ends up getting spectacularly drunk, and Dean vaguely remembers Cas fucking him in the bathroom stall in the club. When Ruby catches them on their way out, she laughs, “You’ll fit right in here!”

Dean thinks that yeah, he will.


End file.
